Aralkylphenylureas and herbicides containing these

ABSTRACT

Aralkylphenylureas of the formula ##STR1## wherein R 1  and R 2  are hydrogen, alkoxy or unsubstituted or substituted alkyl, cycloalkyl, alkenyl or alkynyl, or R 1  and R 2  together are unsubstituted or substituted alkylene which may or may not be interrupted by oxygen or sulfur, Y is hydrogen, alkyl, halogen, alkoxy or haloalkyl, A is unsubstituted or substituted alkylene, Z is hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, halogen, a C 4  H 4  chain which is fused to the benzene ring to give a substituted or unsubstituted naphthyl ring, alkoxy, haloalkoxy, alkylthio, thiocyanato, cyano, ##STR2## R&#39; and R&#34; being hydrogen, alkyl, alkoxy, alkylthio, cycloalkyl or unsubstituted or substituted phenyl and n is 1, 2, 3 or 4, and herbicides containing these ureas.

This is a division of application Ser. No. 268,120, filed May 28, 1981 pending.

The present invention relates to novel, valuable aralkylphenylureas having a herbicidal action, processes for the preparation of these compounds, herbicides containing these compounds, and methods of control of undesired plant growth by means of these compounds.

It is known from German Laid-Open Application DE-OS No. 2,846,723 that aralkoxyphenylureas, for example 1-(3-(2-phenylethoxy)-phenyl)-3-methoxy-3-methylurea, have herbicidal properties.

We have found that aralkylphenylureas of the formula ##STR3## where R¹ and R² are hydrogen, alkoxy or unsubstituted or halogen-, alkoxy- or cyano-substituted alkyl, cycloalkyl, alkenyl or alkynyl, or R¹ and R² together are unsubstituted or alkyl-substituted alkylene which may or may not be interrupted by oxygen or sulfur, Y is hydrogen, alkyl, halogen, alkoxy or haloalkyl, A is unsubstituted or alkyl-substituted alkylene, Z is hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, halogen, a C₄ H₄ chain which is fused to the benzene ring to give a substituted or unsubstituted naphthyl ring, alkoxy, haloalkoxy, alkylthio, thiocyanato, cyano, ##STR4## R' and R" each, independently of one another, being hydrogen, alkyl, alkoxy, alkylthio, cycloalkyl or unsubstituted or alkyl-, halogen- or alkoxy-substituted phenyl and n is 1, 2, 3 or 4, exert a good herbicidal action on numerous important undesired plants, and are well tolerated by various crops.

Examples of possible meanings of the radicals shown in the general formula are:

R¹ and R² (independently of one another): hydrogen, alkoxy (eg. methoxy or ethoxy), unsubstituted or halogen-, alkoxy- or cyano-substituted alkyl (eg. methyl, ethyl, isopropyl, n-propyl, n-butyl, sec.-butyl, tert.-butyl, n-butyl, iso-butyl, sec.-pentyl, 2-chloroethyl, 2-methoxyethyl and 2-cyanomethyl), cycloalkyl, alkenyl or alkynyl (eg. cyclopropyl, cyclohexyl, sec.-butynyl, propargyl and allyl).

R¹ and R² together: unsubstituted or alkyl-substituted alkylene of 2 to 8 carbon atoms which can be interrupted by oxygen or sulfur (eg. propylene, butylene, pentylene, hexylene, 1,4-dimethylbutylene, 3-oxapentylene and 3-thiopentylene).

Y: hydrogen, alkyl (eg. methyl and t-butyl), halogen (eg. fluorine, chlorine and bromine), alkoxy (eg. methoxy) and haloalkyl (eg. trifluoromethyl).

A: unsubstituted or alkyl-substituted alkylene of 1 to 10 carbon atoms (eg. methylene, methylmethylene, dimethylmethylene, propylene, hexylene, ethylene, methylethylene, methylpropylene, ethylpropylene, butylene, pentylene, methylpentylene, dimethylpropylene, heptylene, ethylbutylene and trimethylpentylene).

Z: hydrogen, alkyl (eg. methyl, ethyl and t-butyl), haloalkyl (eg. trifluoromethyl), alkoxyalkyl (eg. methoxymethyl), cycloalkyl (eg. cyclohexyl), aralkyl (eg. benzyl), aryl (eg. phenyl), aryloxy (eg. phenoxy), halogen (eg. fluorine, chlorine, bromine or iodine), a C₄ H₄ chain which is fused to the benzene ring to give an unsubstituted or substituted naphthyl ring, alkoxy (eg. isopropoxy and hexoxy), haloalkoxy (eg. 1,1,2,2-tetrafluoroethoxy), alkylthio (eg. methylthio), thiocyanato, cyano, ##STR5## where R' and R" are each, independently of one another, hydrogen, alkyl (eg. methyl or ethyl), alkoxy (eg. methoxy or tert.-butoxy), alkylthio (eg. methylthio), cycloalkyl (eg. cyclohexyl) or unsubstituted or alkyl-, halogen- or alkoxy-substituted phenyl (eg. phenyl, 3-chlorophenyl, 4-methylphenyl or 3-methoxyphenyl).

The novel compounds can be prepared by, for example, the following processes:

Process I

An aralkylphenyl isocyanate of the formula ##STR6## where Y, A and (Z)_(n) have the above meanings, is reacted with an amine of the general formula ##STR7## where R¹ and R² are as defined above.

The reaction of the aralkylphenyl isocyanate is carried out with or without a conventional catalyst for isocyanate reactions, for example a tertiary amine (eg. triethylamine or 1,4-diazabicyclo-(2,2,2)-octane), a nitrogen-containing heterocyclic (eg. pyridine or 1,2-dimethylimidazole) or an organic tin compound (dibutyltin diacetate or dimethyl-tin dichloride), in the presence or absence of a solvent which is inert under the reaction conditions, for example a hydrocarbon (eg. naphtha, gasoline, toluene, pentane or cyclohexane), a halohydrocarbon (eg. methylene chloride, chloroform, dichloroethane, chlorobenzene or o-, m- or p-dichlorobenzene), a nitrohydrocarbon (eg. nitrobenzene or nitromethane), a nitrile (eg. acetonitrile, butyronitrile or benzonitrile), an ether (eg. diethyl ether, tetrahydrofuran or dioxane), an ester (eg. ethyl acetate or methyl propionate), a ketone (eg. acetone or methyl ethyl ketone) or an amide (dimethylformamide or formamide), at from 0° to 150° C., preferably from 40° to 100° C. (cf. S. Petersen in Methoden der Organ.Chemie, Volume VIII, page 132, Georg-Thieme-Verlag, Stuttgart, 4th edition (1952)).

Process II

An aralkylaniline of the formula ##STR8## where Y, A and (Z)_(n) have the above meanings, is reacted with an isocyanate of the general formula

    R.sup.1 --NCO,

where R¹ has the above meanings. This process is carried out like process I and only gives compounds where R² is hydrogen.

Process III

An aralkylaniline of the formula ##STR9## where Y, A and (Z)_(n) have the above meanings, is reacted with a compound of the general formula ##STR10## where R¹ and R² are as defined above. The reaction is carried out with or without a suitable solvent (see Process I), in the presence of a conventional acid acceptor, for example an alkali metal hydroxide, carbonate or bicarbonate, an alkaline earth metal oxide, hydroxide, carbonate or bicarbonate, or a tertiary organic base (eg. triethylamine, pyridine, N,N-dimethylaniline, N,N-dimethylcyclohexylamine, quinoline or tributylamine), at from -20° to 150° C., preferably from 20° to 80° C.

To prepare the aralkylphenyl isocyanates required in Process I, an aralkylaniline of the formula shown under Process II is reacted, by conventional methods, with phosgene (W. Siefken, J. Liebigs Annalen der Chemie 562 (1949), 75 et seq.). To prepare the aralkylanilines required in Process II, a nitrobenzene of the general formula ##STR11## where D is a saturated or unsaturated, unsubstituted or alkyl-substituted alkylene chain, which may or may not be interrupted by a keto group, or D is a keto group, and Y and (Z)_(n) have the above meanings, is catalytically hydrogenated, using a conventional hydrogenation catalyst (for example palladium on charcoal, platinum sponge or Raney nickel), a suitable solvent, such as a carboxylic acid (eg. acetic acid), an ether (eg. tetrahydrofuran) or an alcohol (eg. ethanol), and, where appropriate, a strong acid (eg. methanesulfonic acid or sulfuric acid), at from 0° to 150° C. and under a pressure of from 1 to 100 bar (B. R. Baker et al., J.Pharm.Sci. 56 (1967), 737-742).

The required nitrobenzenes can be prepared by conventional processes (cf., for example, B. R. Baker et al., loc. cit.; P. Pfeiffer et al., J.Prakt.Chem. 109 (1925), 41; R. Geigy and W. Koenigs, Chem.Ber. 18 (1885), 2401-2407; P. Petrenko-Kritshenko, Chem.Ber. 25 (1892), 2239-2242).

The Examples which follow illustrate the preparation of the novel aralkylaniline derivatives and of their intermediates.

Method A 3-(3-Phenylpropyl)-phenyl isocyanate

170 g of phosgene are dissolved in 200 ml of toluene at -10° C. At the same temperature, 145 g of 3-(3-phenylpropyl)-aniline in 300 ml of toluene are then slowly added dropwise. The mixture is warmed slowly, the introduction of phosgene is started when 60° C. is reached, and the mixture is brought to the boil. After 6 hours, excess phosgene is flushed out with nitrogen and the mixture is distilled. 156 g of 3-(3-phenylpropyl)-phenyl isocyanate, of boiling point 107°-110° C./0.1 mbar, are obtained.

Method B 3-(3-Phenylpropyl)-aniline

253 g of 1-phenyl-3-(3'-nitrophenyl)-prop-2-en-1-one are suspended in 2.5 liters of glacial acetic acid. 196 g of concentrated sulfuric acid and 10 g of 10% strength Pd on animal charcoal are added and the mixture is hydrogenated under 1.1 bar hydrogen pressure at 65°-70° C., until no further hydrogen is absorbed. When the mixture has cooled, some of the acetic acid is distilled off, the residue is rendered alkaline with sodium hydroxide solution and extracted by shaking with ether, the organic phase is dried over sodium sulfate and filtered, the solvent is stripped off and the residue is distilled. 150 g of 3-(3-phenylpropyl)-aniline of boiling point 148° C./0.2 mbar are obtained.

The following aralkylanilines can be prepared correspondingly: 3-benzylaniline (melting point 43°-45° C.), 3-(3-(2-chlorophenyl)-propyl)-aniline (boiling point 156°-158° C./0.1 mbar), 3-(3-(4-chlorophenyl)-propyl)-aniline (boiling point 160°-161° C./0.1 mbar), 3-(3-(2-methoxyphenyl)-propyl)-aniline (boiling point 168°-170° C./0.3 mbar), 3-(3-(3-methoxyphenyl)-propyl)-aniline (boiling point 181°-182° C./0.4 mbar), 3-(3-(3-methylphenyl)-propyl)-aniline (boiling point 142°-145° C./0.01 mbar), 3-(3-(4-methylphenyl)-propyl)-aniline (boiling point 148°-150° C./0.1 mbar), 3-(3-(3-trifluoromethylphenyl)-propyl)-aniline (boiling point 142°-145° C./0.3 mbar), 3-(3-(4-fluorophenyl)-propyl)-aniline (boiling point 125°-127° C./0.1 mbar), 3-(3-(4-tert.-butylphenyl)-propyl)-aniline (boiling point 180°-185° C./0.4 mbar), 3-(3-(4-phenylphenyl)-propyl)-aniline (melting point 76°-77° C.), 3-(3-(4-ethylphenyl)-propyl)-aniline (boiling point 165°-168° C./0.2 mbar), 3-(3-(3-chlorophenyl)-propyl)-aniline (boiling point 165°-172° C./0.4 mbar), 3-(3-(3-hydroxyphenyl)-propyl)-aniline (melting point 59°-61° C.), 3-(3-(3,4-dimethoxyphenyl)-propyl)-aniline (boiling point 195° C./0.15 mbar), 3-(3-(4-methoxyphenyl)-propyl)-aniline (boiling point 176° C./0.1 mbar), 4-(3-phenylpropyl)-aniline (boiling point 156°-157° C./0.4 mbar), 3-(2-methyl-3-phenyl-propyl)-aniline (boiling point 152°-153° C./0.4 mbar), 3-(2-methyl-3-(4-fluorophenyl)-propyl)-aniline, 3-(4-methyl-5-phenyl-pentyl)-aniline (boiling point 177°-179° C./0.3 mbar), 3-(2-ethyl-3-phenyl-propyl)-aniline (boiling point 158°-162° C./0.2 mbar), 4-(3-(4-methylphenyl)-propyl)-aniline (melting point 53°-56° C.), 3-(3-phenylpropyl)-4-bromoaniline (boiling point 159°-160° C./0.1 mbar), 4-(3-(5-fluorophenyl)-propyl)-aniline (boiling point 146°-147° C./0.1 mbar), 4-(3-(2-methylphenyl)-propyl)-aniline (boiling point 160°-162° C./0.1 mbar), 4-(3-(3-methylphenyl)-propyl)-aniline, 4-(4'-phenyl)-benzylaniline (melting point 105°-107° C.), 4-benzylaniline (melting point 35°-37° C.), 4-(3-(3-methoxyphenyl)-propyl)-aniline (boiling point 178°-180° C./0.1 mbar), 4-(2-phenylethyl)-aniline (melting point 42°-45° C.), 3-(2-phenylethyl)-aniline (melting point 50°-52° C.), 4-(4-phenylbutyl)-aniline (oil), 3-(4-phenylbutyl)-aniline (oil), 3-(3-(2-methylphenyl)-propyl)-aniline (boiling point 150°-153° C./0.2 mbar), 3-(3-(3-phenoxyphenyl)-propyl)-aniline (boiling point 195° C./0.2 mbar), 3-(3-(4-ethoxyphenyl)-propyl)-aniline (boiling point 177° C./0.3 mbar), 3-(3-tetrafluoroethoxy-phenyl)-propyl)-aniline (boiling point 155° C./0.1 mbar), 3-(3-(4-chlorophenyl)-propyl)-aniline (boiling point 150°-154° C./0.1 mbar), 3-(3-(3,4-dichlorophenyl)-propyl)-aniline (boiling point 177°-182° C./0.1 mbar) and 3-(3-(α-naphthyl)-propyl)-aniline.

EXAMPLE 1

11 g of 2,5-dimethylpyrrolidine are added dropwise to a mixture of 23.7 g of 3-(3-phenylpropyl)-phenyl isocyanate and 200 ml of toluene at 0° C. After it has been stirred for 6 hours, the mixture is concentrated and the residue is stirred with petroleum ether. 25.1 g of white crystals of melting point 86°-88° C. are obtained; the product has the following structural formula (active ingredient No. 1) ##STR12##

EXAMPLE 2

7.6 g of N-methyl-N-methoxycarbamyl chloride are added dropwise to a mixture of 15 g of 3-(3-(4-chlorophenyl)-propyl)-aniline, 8 g of NaHCO₃ and 200 ml of THF at 20° C. and the mixture is stirred overnight. After the solution has been filtered and concentrated, the residue is chromatographed over silica gel, using a mixture of 90 parts of toluene and 10 parts of ethyl acetate. 14.6 g of a product, of melting point 73°-76° C., having the following structural formula are obtained (active ingredient No. 2): ##STR13##

EXAMPLE 3

A mixture of 42.2 g of 3-(3-phenylpropyl)-aniline, 12.2 g of methyl isocyanate, 2 drops of dibutyltin diacetate and 400 ml of THF is left to stand for 4 days at 20° C. and is then concentrated, and the residue is triturated with petroleum ether. 53 g of a white substance, of melting point 104°-106° C., are obtained. The product has the following structural formula (active ingredient No. 3): ##STR14##

The following compounds can also be prepared in accordance with one of the above processes:

    __________________________________________________________________________      No.                                                                                ##STR15##  Y   A           (Z).sub.n     M.p. °C.                  __________________________________________________________________________     4   NHCH.sub.3 H   3-CH.sub.2  H             153-154                           5   "          "   3(CH.sub.2).sub.2                                                                          "                                               6   "          "   4(CH.sub.2).sub.3                                                                          "             107-110                           7   "          3Cl "           "                                               8   N(CH.sub.3).sub.2                                                                         "   3(CH.sub.2).sub.3                                                                          "             106-108                           9   N(OCH.sub.3)CH.sub.3                                                                      "   "           "             60-63                             10  NH cycl.C.sub.3 H.sub.5                                                                   "   "           "             113-115                           11  N(C.sub.2 H.sub.5).sub.2                                                                  "   "           "             85-87                             12  N(C.sub.2 H.sub.5)(nC.sub.4 H.sub.9)                                                      "   "           "             oil                               13  NHC.sub.2 H.sub.5                                                                         "   "           "             83-85                             14                                                                                  ##STR16## "   "           "             88-90                             15                                                                                  ##STR17## "   "           "             112-114                           16                                                                                  ##STR18## "   "           "             111-113                           17  N(CH.sub.3) cycl.C.sub.6 H.sub.11                                                         "   "           "             135-137                           18  NHCH.sub.2 CH.sub.2 Cl                                                                    "   "           "                                               19  NH iso C.sub.3 H.sub.7                                                                    "   "           "                                               20  NHCH.sub.2 CH.sub.2 OCH.sub.3                                                             "   "           "                                               21  NHCH.sub.2 CH.sub.2 CN                                                                    "   "           "                                               22  NHCH.sub.3 "   "           3OCH.sub.3    84-85                             23  "          "   "           4Cl           147-148                           24  "          "   "           3NHCONHCH.sub.3                                 25  "          4OCH.sub.3                                                                         "           4SCN                                            26  "          "   "           4CH.sub.2 OCH.sub.3                             27  "          4CH.sub.3                                                                          "           3CN                                             28  "          "   "           4cyclC.sub.5 H.sub.9                            29  "          H   3(CH.sub.2).sub.4                                                                          H                                               30  "          "   "           4CH.sub.2 C.sub.6 H.sub.5                       31  "          4Cl 3(CH.sub.2).sub.3                                                                          H                                               32  N(CH.sub.3).sub.2                                                                         "   "           "                                               33  NHCH.sub.3 H   "           4-tert.C.sub.4 H.sub.9                                                                       123-125                           34  "          "   "           3Br                                             35  "          "   "           3OisoC.sub.3 H.sub.7                            36  "          "   "           3OC.sub.2 H.sub.4                               37  "          "   "           4OCH.sub.3                                      38  "          "   "           4F            129-130                           39  "          "   "           3OCHF.sub.2                                     40  "          "   "           4SCH.sub.3                                      41  "          "   "           4N(CH.sub.3).sub.2                              42  "          "   "           3,4Cl.sub.2                                     43  "          "   "           2,5Cl.sub.2                                     44  "          "   "           2,4Cl.sub.2                                     45  "          "   "           2,4(CH.sub.3).sub.2                             46  "          "   "           4C.sub.6 H.sub.5                                                                             156-158                           47  "          "   "           3CH.sub.3     104-105                           48  "          "   "           4CH.sub.3     124-125                           49  "          "   "           4Br                                             50  "          "   "           3COOC.sub.2 H.sub.5                             51  "          "   "           3Cl                                             52  "          "   "           2Cl                                             53  "          "   "           2CH.sub.3                                       54  "          "   "           2OCH.sub.3                                      55  "          "   "           2,3(CHCHCHCH)                                   56  "          "   "           3CF.sub.3     125-126                           57  "          "   3CH.sub.2 CH(CH.sub.3)CH.sub.2                                                             H             82-84                             58  "          "   "           4F                                              59  "          "   3(CH.sub.2).sub.3 CH(CH.sub.3)CH.sub.2                                                     H             oil                               60  "          "   3CH.sub.2 CH(C.sub.2 H.sub.5)CH.sub.2                                                      "             oil                               61  N(CH.sub.3).sub.2                                                                         "   3(CH.sub.2).sub.3                                                                          2Cl                                             62  "          "   "           3Cl                                             63  "          "   "           4Cl                                             64  "          "   "           2,4Cl.sub.2                                     65  "          "   "           2,5Cl.sub.2                                     66  "          "   "           3,4Cl.sub.2                                     67  "          "   "           2CH.sub.3                                       68  "          "   "           3CH.sub.3                                       69  "          "   "           4CH.sub.3                                       70  "          "   "           2,4(CH.sub.3).sub.2                             71  "          "   "           3,4(CH.sub.3).sub.2                             72  "          "   "           3OCH.sub.3                                      73  "          "   "           4OCH.sub.3                                      74  "          "   "           3OisoC.sub.3 H.sub.7                            75  "          "   "           4C.sub.2 H.sub.5                                76  "          "   "           4C.sub.6 H.sub.5                                77  "          "   "           3CF.sub.3                                       78  "          "   "           4Br                                             79  N(OCH.sub.3)CH.sub.3                                                                      "   "           2Cl                                             80  "          "   "           3Cl           46-48                             81  "          "   "           2,4Cl.sub.2                                     82  "          "   "           3,4Cl.sub.2   54-56                             83  "          "   "           2,5Cl.sub.2                                     84  "          "   "           2CH.sub.3     88-90                             85  "          "   "           3CH.sub.3                                       86  "          "   "           4CH.sub.3     68-71                             87  "          "   "           2,4(CH.sub.3).sub.2                             88  "          "   "           3,4(CH.sub.2).sub.3                             89  "          "   "           3OCH.sub.3    76-77                             90  "          "   "           4OCH.sub.3                                      91  "          "   "           4C.sub.6 H.sub. 5                               92  "          "   "           3CF.sub.3                                       93  "          "   "           2,3(CHCHCHCH) 93-95                             94  "          "   4(CH.sub.2).sub.3                                                                          4CH.sub.3     58-60                             95  N(CH.sub.3).sub.2                                                                         "   "           "             138-139                           96  "          3Cl "           "                                               97  NHCH.sub.3 H   3(CH.sub.2).sub.3                                                                          4C.sub.2 H.sub.5                                                                             109-111                           98  "          "   "           3OH           80-82                             99  "          4Br "           H             156-158                           100                                                                                 ##STR19## "   3-CH.sub.2CH.sub.2CH.sub.2                                                                 "             72-74                             101 "          H   "           4-OC.sub.2 H.sub.5                                                                           55-57                             102 "          "   "           3-OCF.sub.2 CHF.sub.2                                                                        oil                               103 "          "   "           3,4-CHCHCHCH                                    104 NHCH.sub.3 "   "           4-OC.sub.2 H.sub.5                                                                           93-95                             105                                                                                 ##STR20## "   "           H             65-67                             106                                                                                 ##STR21## "   "           "             90-92                             107 NHCH.sub.3 "   4-CH.sub.2CH.sub.2CH.sub.2                                                                 4-CH.sub.3    139-142                           108                                                                                 ##STR22## "   "           H             oil                               109 "          "   3-CH.sub.2CH.sub.2CH.sub.2                                                                  ##STR23##    oil                               110                                                                                 ##STR24## "   4CH.sub.2 CH.sub.2 CH.sub.2                                                                4F            92-94                             111 "          "   "           4Otert.Butyl                                    112 "          "   "           4C.sub.2 H.sub.5                                113 "          "   "           4-tert.Butyl                                    114 "          "   "           4Cl           76-77                             115 "          "   "           4NHCOCH.sub.3                                   116 "          "   "           4N(C.sub.2 H.sub.5).sub.2                       117 "          "   "           4N(CH.sub.3).sub.2                                                                           59-61                             118 "          "   "           4OC.sub.6 H.sub.13                              119 "          "   "           2Cl                                             120 "          "   "           3Cl                                             121 "          "   "           4-isopropyl   oil                               122 "          "   "           3-phenoxy     oil                               123 "          "   "           4-phenyl      82-84                             124 "          "   "           3OC.sub.2 H.sub.5                               125 "          "   "           2CH.sub.3     oil                               126 "          "   "           3CH.sub.3     40                                127 "          "   "           2CF.sub.3                                       128 "          "   "           3CF.sub.3     63-65                             129 "          "   "           4CF.sub.3                                       130 "          "   "           2OCH.sub.3                                      131 "          "   "           3OCH.sub.3    82-84                             132 "          "   "           4OCH.sub.3    68-70                             133 "          "   "           2,4,6(CH.sub.3).sub.3                           134 "          "   "           3,4Cl.sub.2                                     135 "          "   "           3OH                                             136 "          "   "           3OSO.sub.2 CH.sub.3                             137 "          "   "           2,4(CH.sub.3).sub.2                             138 "          "   "           3OCH.sub.2phenyl                                139 "          "   "           2F                                              140 "          "   "           4OC.sub.2 H.sub.5                               141                                                                                 ##STR25## "   "           H                                               142                                                                                 ##STR26## "   "           "                                               143 N(C.sub.2 H.sub.5).sub.2                                                                  "   "           "                                               144                                                                                 ##STR27## "   "           "                                               145 "          "   "           4CH.sub.3                                       146 "          "   "           4F                                              147 "          "   "           4Cl                                             148                                                                                 ##STR28## "   "           4CH.sub.3     118-119                           149 "          "   "           4F                                              150 "          "   "           4Cl                                             151 NHC.sub.2 H.sub.5                                                                         "   "           4CH.sub.3                                       152 N(CH.sub.3).sub.2                                                                         "   "           "                                               153                                                                                 ##STR29## "   "           "             104-106                           154                                                                                 ##STR30## "   "           "             129-130                           155                                                                                 ##STR31## "   "           "             128-130                           156 N(C.sub.2 H.sub.5).sub.2                                                                  "   "           "             70-72                             157 NHOCH.sub.3                                                                               "   "           "                                               158 NHOC.sub.2 H.sub.5                                                                        "   "           "                                               159 NHCH.sub.2 CHCH.sub.2                                                                     "   "           "             127-128                           160 N(CH.sub.3)C.sub.4 H.sub.9                                                                "   "           "             75-76                             161 NHC(CH.sub.3).sub.2 CCH                                                                   "   "           "                                               162 N(CH.sub.3).sub.2                                                                         "   "           4Cl                                             163 "          "   "           4F                                              164 "          "   "           4OCH.sub.3 "                                    165 N(OCH.sub.3)CH.sub.3                                                                      "   3CH.sub.2 CH.sub.2 CH.sub.2                                                                 ##STR32##    98-100                            166 "          "   4CH.sub.2   H             86-88                             167 "          "   "           4-phenyl      117-120                           168 "          3CF.sub.3                                                                          4CH.sub.2 CH.sub.2 CH.sub.2                                                                H                                               169 "          H   4(CH.sub. 2).sub.5                                                                         "                                               170 "          "   4CH(CH.sub.3)CH.sub.2                                                                      "                                               171 "          "   4CH.sub.2 CH(CH.sub.3)                                                                     "                                               172 "          "   4C(CH.sub.3).sub.2                                                                         "                                               173 "          "                                                                                   ##STR33##  "                                               174 "          "   "           4OCH.sub.3                                      175 "          "                                                                                   ##STR34##  H             oil                               176 "          "                                                                                   ##STR35##  "                                               177 "          "                                                                                   ##STR36##  "                                               178 "          "   "           4CH.sub.3                                       179 "          "                                                                                   ##STR37##  4F            oil                               180 "          "                                                                                   ##STR38##  H             54-56                             181 "          "   "           4CH.sub.3     67-69                             182                                                                                 ##STR39## "                                                                                   ##STR40##  4Cl           oil                               183 "          "                                                                                   ##STR41##  H                                               184 "          "   3CH.sub.2CH.sub.2                                                                          "             100-103                           185 "          "   4CH.sub.2 CH.sub.2 CH.sub.2                                                                3COphenyl                                       186 "          "   "           3,5Cl.sub.2 4CH.sub.3                           187 "          "   "           4NHCOCH.sub.3                                   188 "          "   "           4NHCOOC.sub.2 H.sub.5                           189 "          "   "           4NHCOphenyl                                     190 "          "   "           3CON(C.sub.2 H.sub.5).sub.2                     191 "          "   "           3SO.sub.2phenyl                                 192 "          "   "           4COC.sub.2 H.sub.5                              193 "          "   "           3SO.sub.2 N(CH.sub.3).sub.2                     194 "          "   4CH.sub.2 CH.sub.2                                                                         H             88-92                             195 "          "   4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                       "             90-92                             196 "          "   3CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                       "             51                                197 N(CH.sub.3).sub.2                                                                         "   "           "                                               198 "          "   4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                                       "                                               199 "          "   3CH.sub.2 CH.sub.2                                                                         "                                               200 "          "   4CH.sub.2   "                                               201 "          "   4CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                              "                                               202 "          "                                                                                   ##STR42##  "                                               203 "          "   3CH.sub.2C(CH.sub.3).sub.2 CH.sub.2                                                        "                                               204 "          "   4CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2                                                       "                                               __________________________________________________________________________

The novel active ingredients can be converted into the conventional formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends entirely on the purpose for which the agents are being used; it should, however, ensure a fine and uniform distribution of the active ingredient. The formulations are prepared in the conventional manner, for example by diluting the active ingredient with solvent and/or carriers, with or without the addition of emulsifiers and dispersants and, where water is used as the diluent, with or without organic auxiliary solvents. Suitable auxiliaries are, essentially, solvents, for example aromatics, e.g., xylene and benzene, chloroaromatics, e.g. chlorobenzene, paraffins, e.g. petroleum fractions, alcohols, e.g. methanol and butanol, amines e.g., ethanolamine, dimethylformamide, and water; solid carriers, for example natural rock powders, e.g., kaolin, alumina, talc and chalk, and synthetic rock powders, e.g. highly disperse silica and silicates; emulsifiers, for example non-ionic and anionic emulsifiers, e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates, and dispersants, for example lignin, sulfite waste liquors and methylcellulose.

The agents in general contain from 0.1 to 95% by weight of active ingredient, preferably from 5 to 90%.

The agents, and the ready-to-use preparations obtained therefrom, e.g., solutions, emulsions, suspensions, powders, dusts, pastes or granules, are applied in conventional manner, e.g. by spraying, atomizing, dusting, broadcasting or watering.

EXAMPLE I

90 parts by weight of compound 1 is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE II

10 parts by weight of compound 2 is dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 2 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.

EXAMPLE III

20 parts by weight of compound 2 is dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol, and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.

EXAMPLE IV

20 parts by weight of compound 3 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.

EXAMPLE V

80 parts by weight of compound 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill.

EXAMPLE VI

5 parts by weight of compound 1 is intimately mixed with 95 parts by weight of particulate kaolin. A dust is obtained containing 5% by weight of the active ingredient.

EXAMPLE VII

30 parts by weight of compound 1 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

EXAMPLE VIII

40 parts by weight of compound 1 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable, aqueous dispersion is obtained.

EXAMPLE IX

20 parts of compound 1 is intimately mixed with 12 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The influence of various representatives of the novel aralkylphenylureas on the growth of unwanted and crop plants is demonstrated in greenhouse experiments.

The vessels employed were plastic flowerpots having a volume of 300 cm³, and which were filled with a sandy loam containing about 1.5% humus. The seeds of the test plants were sown shallow, and separately, according to species.

In the preemergence treatment, the active ingredients were immediately applied to the surface of the soil as a suspension or emulsion in water by spraying through finely distributing nozzles. The amount of active ingredient applied in this treatment was equivalent to 3.0 kg/ha.

After the agents had been applied, the vessels were lightly sprinkler-irrigated to induce germination and growth and to activate the chemical agents. Transparent plastic covers were then placed on the vessels until the plants had taken root. The cover ensured uniform germination of the plants, insofar as this was not impaired by the chemicals.

For the postemergence treatment, the plansts were first grown in the vessels to a height of from 3 to 10 cm, depending on growth form, before being treated. For this treatment, either plants which had been sown directly in the pots and had grown there were selected, or plants which had been grown separately as seedlings and transplanted to the experiment vessels a few days before treatment. The amount of active ingredient applied in this treatment was equivalent to 0.25 kg/ha.

The comparative agent was 1-(3-(2-phenylethoxy)-phenyl)-3-methoxy-3-methylurea (A), applied at the same rates.

No cover was placed on the vessels in the postemergence treatment. The pots were set up in the greenhouse-species from warmer areas at from 20° to 30° C., and species from moderate climates at 15° to 25° C. The experiments were run for from 2 to 4 weeks. During this period, the plants were tended and their reactions to the various treatments assessed. The scale used for assessment was 0 to 100, 0 denoting no damage or normal emergence, and 100 denoting nonemergence or complete destruction of at least the visible plant parts.

The results obtained show that new compound no. 2 is, on postemergence application in the greenhouse, tolerated by cereals better than prior art comparative agent (A). On preemergence application in the greenhouse, active ingredients 4, 8, 9, 14, 38, 47 and 57 have a herbicidal action which is mostly very good.

On postemergence application in the greenhouse, active ingredients 3 and 86 have, at a rate of 0.25 kg/ha, a better selective herbicidal action than prior art compound A. On postemergence application in the greenhouse, a good selective herbicidal action was exhibited by active ingredient no. 16 at 0.5 kg/ha, active ingredient no. 100 at 0.25 kg/ha and active ingredient no. 22 at 0.25 kg/ha. On postemergence application in the greenhouse, active ingredient no. 9 exhibited, at 0.25 kg/ha, a better selective herbicidal action than the prior art active ingredient 1-(3-(3-phenoxyethoxy)-phenyl)-3-methoxy-3-methylurea (B) (German Laid-Open Application DE-OS No. 2,846,723). On postemergence application in the greenhouse, active ingredient no. 8 exhibited, at 0.25 kg/ha, a better selective herbicidal action than the prior art active ingredient 1-(3-(2-phenoxyethoxy)-phenyl)-3,3-dimethylurea (C) (German Laid-Open Application DE-OS No. 2,846,723) at a rate of 2 kg/ha.

On postemergence treatment in the greenhouse, active ingredients nos. 84, 80, 102, 104, 101 and 109 exhibited, at 0.125 and 0.5 kg/ha, a better selective herbicidal action than the prior art active ingredient 1-(3-(2-(2,4-dichloro)-phenoxyethoxy)-phenyl)-3-methoxy-3-methylurea (D) (German Laid-Open Application DE-OS No. 2,846,723) at 0.5 kg/ha. On postemergence application in the greenhouse, active ingredient no. 94 exhibited, at 0.25 kg/ha, a better selective herbicidal action than prior art active ingredient 1-(4-(2-(4-methyl)-phenoxyethyl)-phenyl)-3-methoxy-3-methylurea (E) (German Laid-Open Application DE-OS No. 2,846,723).

If certain crop plants tolerate the active ingredients less well, application techniques may be used in which the agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

In view of the good tolerance of the active ingredients and the many application methods possible, the agents according to the invention may be used in a large range of crops for removing unwanted plants.

Application rates may vary from 0.1 to 15 kg/ha and more.

The following crop plants may be mentioned by way of example:

    ______________________________________                                         Botanical name    Common name                                                  ______________________________________                                         Allium cepa       onions                                                       Ananas comosus    pineapples                                                   Arachis hypogaea  peanuts (groundnuts)                                         Asparagus officinalis                                                                            asparagus                                                    Avena sativa      oats                                                         Beta vulgaris spp. altissima                                                                     sugarbeets                                                   Beta vulgaris spp. rapa                                                                          fodder beets                                                 Beta vulgaris spp. esculenta                                                                     table beets, red beets                                       Brassica napus var. napus                                                                        rape                                                         Brassica napus var. napobrassica                                               Brassica napus var. rapa                                                                         turnips                                                      Brassica rapa var. silvestris                                                  Camellia sinensis tea plants                                                   Carthamus tinctorius                                                                             safflower                                                    Carya illinoinensis                                                                              pecan trees                                                  Citrus limon      lemons                                                       Citrus maxima     grapefruits                                                  Citrus reticulata                                                              Citrus sinensis   orange trees                                                 Coffea arabica (Coffea canephora,                                                                coffee plants                                                Coffea liberica)                                                               Cucumis melo      melons                                                       Cucumis sativus   cucumbers                                                    Cynodon dactylon  Bermudagrass in turf                                                           and lawns                                                    Daucus carota     carrots                                                      Elais guineensis  oil palms                                                    Fragaria vesca    strawberries                                                 Glycine max       soybeans                                                     Gossypium hirsutum                                                                               cotton                                                       (Gossypium arboreum                                                            Gossypium herbaceum                                                            Gossypium vitifolium)                                                          Helianthus annuus sunflowers                                                   Helianthus tuberosus                                                           Hevea brasiliensis                                                                               rubber plants                                                Hordeum vulgare   barley                                                       Humulus lupulus   hops                                                         Ipomoea batatas   sweet potatoes                                               Juglans regia     walnut trees                                                 Lactuca sativa    lettuce                                                      Lens culinaris    lentils                                                      Linum usitatissimum                                                                              flax                                                         Lycopersicon lycopersicum                                                                        tomatoes                                                     Malus spp.        apple trees                                                  Manihot esculenta cassava                                                      Medicago sativa   alfalfa (lucerne)                                            Mentha piperita   peppermint                                                   Musa spp.         banana plants                                                Nicothiana tabacum                                                                               tobacco                                                      (N. rustica)                                                                   Olea europaea     olive trees                                                  Oryza sativa      rice                                                         Panicum miliaceum                                                              Phaseolus lunatus limabeans                                                    Phaseolus mungo   mungbeans                                                    Phaseolus vulgaris                                                                               snapbeans, green beans,                                                        dry beans                                                    Pennisetum glaucum                                                             Petroselinum crispum                                                                             parsley                                                      spp. tuberosum                                                                 Picea abies       Norway spruce                                                Abies alba        fir trees                                                    Pinus spp.        pine trees                                                   Pisum sativum     English peas                                                 Prunus avium      cherry trees                                                 Prunus domestica  plum trees                                                   Prunus dulcis     almond trees                                                 Prunus persica    peach trees                                                  Pyrus communis    pear trees                                                   Ribes sylvestre   redcurrants                                                  Ribe uva-crispa   gooseberries                                                 Ricinus communis  castor-oil plants                                            Saccharum officinarum                                                                            sugar cane                                                   Secale cereale    rye                                                          Sesamum indicum   sesame                                                       Solanum tuberosum Irish potatoes                                               Sorghum bicolor (s. vulgare)                                                                     sorghum                                                      Sorghum dochna                                                                 Spinacia oleracea spinach                                                      Theobroma cacao   cacao plants                                                 Trifolium pratense                                                                               red clover                                                   Triticum aestivum wheat                                                        Vaccinium corymbosum                                                                             blueberries                                                  Vaccinium vitis -idaea                                                                           cranberries                                                  Vicia faba        tick beans                                                   Vigna sinensis (V. unguiculata)                                                                  cow peas                                                     Vitis vinifera    grapes                                                       Zea mays          Indian corn, sweet corn, maize                               ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects, the novel aralkylphenylureas may be mixed among themselves or mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable mixture components are diazines, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl-caramates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, etc. A number of active ingredients which, when combined with the new compounds, give mixtures useful for widely varying applications are given below by way of example:

methyl α-naphthoxyacetate

2-(2-methylphenoxy)-propionic acid (salts, esters, amides)

2-(4-chlorophenoxy)-propionic acid (salts, esters, amides)

2-(2,4-dichlorophenoxy)-propionic acid (salts, esters, amides)

2-(2,4,5-trichlorophenoxy)-propionic acid (salts, esters, amides)

2-(2-methyl-4-chlorophenoxy)-propionic acid (salts, esters, amides)

4-(2,4-dichlorophenoxy)-butyric acid (salts, esters, amides)

4-(2-methyl-4-chlorophenoxy)-butyric acid (salts, esters, amides)

cyclohexyl-3-(2,4-dichlorophenoxy)-acrylate

9-hydroxyfluorenecarboxylic acid-(9) (salts, esters)

2,3,6-trichlorophenylacetic acid (salts, esters)

4-chloro-2-oxobenzothiazolin-3-yl-acetic acid (salts, esters) gibelleric acid (salts)

disodium methylarsonate

monosodium salt of methylarsonic acid

N-phosphonomethyl-glycine (salts)

N,N-bis-(phosphonomethyl)-glycine (salts)

2-chloroethyl 2-chloroethanephosphonate

ammonium-ethyl-carbamoyl-phosphonate

di-n-butyl-1-n-butylamino-cyclohexyl-phosphonate

trithiobutylphosphite

O,O-diisopropyl-5-(2-benzosulfonylaminoethyl)-phosphorodithionate

2,3-dihydro-5,6-dimethyl-1,4-dithiin-1,1,4,4-tetraoxide

5-tert.butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolone-(2)

4,5-dichloro-2-trifluoromethylbenzimidazole (salts)

1,2,3,6-tetrahydropyridazine-3,6-dione (salts)

succinic acid mono-N-dimethylhydrazide (salts)

(2-chloroethyl)-trimethylammonium chloride

(2-methyl-4-phenylsulfonyl)-trifluoromethanesulfone anilide

1,1-dimethyl-4,6-diisopropyl-5-indanyl ethyl ketone

sodium chlorate

ammonium thiocyanate

calcium cyanamide

5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone

5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone

5-amino-4-chloro-2-cyclohexyl-3(2H)-pyridazinone

5-amino-4-bromo-2-cyclohexyl-3(2H)-pyridazinone

5-methylamino-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone

5-methylamino-4-chloro-2-(3-α,α,β,β-tetrafluoroethoxyphenyl)-3(2H)-pyridazinone

5-dimethylamino-4-chloro-2-phenyl-3(2H)-pyridazinone

4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone

4,5-dimethoxy-2-cyclohexyl-3(2H)-pyridazinone

4,5-dimethoxy-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone

5-methoxy-4-chloro-2-(3-trifluoromethylphenyl)-3(2H)-pyridazinone

5-amino-4-bromo-2(3-methylphenyl)-3(2H)-pyridazinone

3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts

3-(1-methylethyl)-8-chloro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts

3-(1-methylethyl)-8-fluoro-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts

3-(1-methylethyl)-8-methyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and salts

1-methoxymethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-methoxymethyl-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-methoxymethyl-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-cyano-8-chloro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-cyano-8-fluoro-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-cyano-8-methyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-cyano-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

1-azidomethyl-3-(1-methylethyl)-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide

3-(1-methylethyl)-1H-pyridino-[3,2-e]-2,1,3-thiadiazin-(4)-one-2,2-dioxide

N-(1-ethylpropyl)-2,6-dinitro-3,4-dimethylaniline

N-(1-methylethyl)-N-ethyl-2,6-dinitro-4-trifluoromethylaniline

N-n-propyl-N-β-chloroethyl-2,6-dinitro-4-trifluoromethylaniline

N-n-propyl-N-cyclopropylmethyl-2,6-dinitro-4-trifluoromethylaniline

N-bis-(n-propyl)-2,6-dinitro-3-amino-4-trifluoromethylaniline

N-bis-(n-propyl)-2,6-dinitro-4-methylaniline

N-bis-(n-propyl)-2,6-dinitro-4-methylsulfonylaniline

N-bis-(n-propyl)-2,6-dinitro-4-aminosulfonylaniline

bis-(β-chloroethyl)-2,6-dinitro-4-methylaniline

N-ethyl-N-(2-methylallyl)-2,6-dinitro-4-trifluoromethylaniline

3,4-dichlorobenzyl N-methylcarbamate

2,6-di-tert.butyl-4-methylphenyl N-methylcarbamate

isopropyl N-phenylcarbamate

3-methoxyprop-2-yl N-3-fluorophenylcarbamate

isopropyl N-3-chlorophenylcarbamate

but-1-yn-3-yl N-3-chlorophenylcarbamate

4-chlorobut-2-yn-1-yl N-3-chlorophenylcarbamate

methyl N-3,4-dichlorophenylcarbamate

methyl N-(4-aminobenzenesulfonyl)-carbamate

O-(N-phenylcarbamoyl)-propanone oxime

N-ethyl-2-(phenylcarbamoyl)-oxypropionic acid amide

3'-N-isopropylcarbamoyloxypropionanilide

ethyl-N-(3-(N'-phenylcarbamoyloxy)-phenyl)-carbamate

methyl-N-(3-(N'-methyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate

isopropyl-N-(3-(N'-ethyl-N'-phenylcarbamoyloxy)-phenyl)-carbamate

methyl-N-(3-(N'-3-methylphenylcarbamoyloxy)-phenyl)-carbamate

methyl-N-(3-(N'-4-fluorophenylcarbamoyloxy)-phenyl)-carbamate

methyl-N-(3-(N'-3-chloro-4-fluorophenylcarbamoxyloxy)-phenyl)-carbamate

ethyl-N-[3-N'-(3-chloro-4-fluorophenylcarbamoyloxy)-phenyl]-carbamate

ethyl-N-[3-N'-(3,4-difluorophenylcarbamoxyloxy)-phenyl]-carbamate

methyl-N-[3-(N'-3,4-difluorophenylcarbamoyloxy)-phenyl]-carbamate

methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylcarbamate

ethyl N-3-(2'-methylphenoxycarbonylamino)-phenylcarbamate

methyl N-3-(4'-fluorophenoxycarbonylamino)-phenylthiolcarbamate

methyl N-3-(2',4',5'-trimethylphenoxycarbonylamino)-phenylthiolcarbamate

methyl N-3-(phenoxycarbonylamino)-phenylthiolcarbamate

p-chlorobenzyl N,N-diethylthiolcarbamate

ethyl N,N-di-n-propylthiolcarbamate

n-propyl N,N-di-n-propylthiolcarbamate

2,3-dichloroallyl N,N-diisopropylthiolcarbamate

2,3,3-trichloroallyl N,N-diisopropylthiolcarbamate

3-methyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate

3-ethyl-5-isoxazolylmethyl N,N-diisopropylthiolcarbamate

ethyl N,N-di-sec.-butylthiolcarbamate

benzyl N,N-di-sec.-butylthiolcarbamate

ethyl N-ethyl-N-cyclohexylthiolcarbamate

ethyl N-ethyl-N-bicyclo-[2.1.1]-heptylthiolcarbamate

S-(2,3-dichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate

S-(2,3,3-trichloroallyl)-(2,2,4-trimethylazetidine)-1-carbothiolate

S-ethylhexahydro-1-H-azepine-1-carbothiolate

S-benzyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate

S-benzyl-(2,3-dimethylhexahydro-1-H-azepine-1)-carbothiolate

S-ethyl-(3-methylhexahydro-1-H-azepine-1)-carbothiolate

n-propyl N-ethyl-N-n-butylthiolcarbamate

2-chloroallyl N,N-dimethyldithiocarbamate

N-methyldithiocarbamic acid, sodium salt

trichloroacetic acid, sodium salt

α,α-dichloropropionic acid, sodium salt

α,α-dichlorobutyric acid, sodium salt

α,α-β,β-tetrafluoropropionic acid, sodium salt

α-methyl-α,β-dichloropropionic acid, sodium salt

methyl α-chloro-β-(4-chlorophenyl)-propionate

methyl α,β-dichloro-β-phenylpropionate

benzamido oxyacetic acid

2,3,5-triiodobenzoic acid (salts, esters, amides)

2,3,6-trichlorobenzoic acid (salts, esters, amides)

2,3,5,6-tetrachlorobenzoic acid (salts, esters, amides)

2-methoxy-3,6-dichlorobenzoic acid (salts, esters, amides)

2-methoxy-3,5,6-trichlorobenzoic acid (salts, esters, amides)

3-amino-2,5,6-trichlorobenzoic acid (salts, esters, amides)

O,S-dimethyltetrachlorothioterephthalate

dimethyl-2,3,5,6-tetrachloroterephthalate

disodium 3,6-endoxohexahydrophthalate

4-amino-3,5,6-trichloropicolinic acid (salts)

ethyl 2-cyano-3-(N-methyl-N-phenyl)-aminoacrylate

isobutyl 2-[4-(4'-chlorophenoxy)-phenoxy]-propionate

methyl 2-[4-(2',4'-dichlorphenoxy)-phenoxy]-propionate

methyl 2-[4-(4'-trifluoromethylphenoxy)-phenoxy]-propionate

2-[4-(2'-chloro-4'-trifluorophenoxy)-phenoxy]-propionic acid, sodium salt

2-[4-(3',5'-dichlorpyridyl-2-oxy)-phenoxy]-propionic acid, sodium salt

ethyl 2-(N-benzoyl-3,4-dichlorophenylamino)-propionate

methyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate

isopropyl 2-(N-benzoyl-3-chloro-4-fluorophenylamino)-propionate

2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine

2-chloro-4-ethylamino-6-(amino-2'-propionitrile)-1,3,5-triazine

2-chloro-4-ethylamino-6-(2-methoxypropyl)-2-amino-1,3,5-triazine

2-chloro-4-ethylamino-6-butyn-1-yl-2-amino-1,3,5-triazine

2-chloro-4,6-bisethylamino-1,3,5-triazine

2-chloro-4,6-bisisopropylamino-1,3,5-triazine

2-chloro-4-isopropylamino-6-cyclopropylamino-1,3,5-triazine

2-azido-4-methylamino-6-isopropylamino-1,3,5-triazine

2-methylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine

2-methylthio-4-ethylamino-6-tert.butylamino-1,3,5-triazine

2-methylthio-4,6-bisethylamino-1,3,5-triazine

2-methylthio-4,6-bisisopropylamino-1,3,5-triazine

2-methoxy-4-ethylamino-6-isopropylamino-1,3,5-triazine

2-methoxy-4,6-bisethylamino-1,3,5-triazine

2-methoxy-4,6-bisisopropylamino-1,3,5-triazine

4-amino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one

4-amino-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one

4-isobutylidenamino-6-tert.butyl-3-methylthio-4,5-dihydro-1,2,4-triazin-5-one

1-methyl-3-cyclohexyl-6-dimethylamino-1,3,5-triazin-2,4-dione

3-tert.butyl-5-chloro-6-methyluracil

3-tert.butyl-5-bromo-6-methyluracil

3-isopropyl-5-bromo-6-methyluracil

3-sec.butyl-5-bromo-6-methyluracil

3-(2-tetrahydropyranyl)-5-chloro-6-methyluracil

3-(2-tetrahydropyranyl)-5,6-trimethyleneuracil

3-cyclohexyl-5,6-trimethyleneuracil

2-methyl-4-(3'-trifluoromethylphenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione

2-methyl-4-(4'-fluorophenyl)-tetrahydro-1,2,4-oxadiazine-3,5-dione

3-amino-1,2,4-triazole

1-allyloxy-1-(4-bromophenyl)-2-[1',2',4'-triazolyl-(1')]-ethane (salts)

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,3-triazol-1-yl)-butan-2-one

N,N-diallylchloroacetamide

N-isopropyl-2-chloroacetanilide

N-(1-methylpropyn-2-yl)-2-chloroacetanilide

2-methyl-6-ethyl-N-propargyl-2-chloroacetanilide

2-methyl-6-ethyl-N-ethoxymethyl-2-chloroacetanilide

2-methyl-6-ethyl-N-(2-methoxy-1-methylethyl)-2-chloroacetanilide

2-methyl-6-ethyl-N-(isopropoxycarbonylethyl)-2-chloroacetanilide

2-methyl-6-ethyl-N-(4-methoxypyrazol-1-yl-methyl)-2-chloroacetanilide

2-methyl-6-ethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide

2,6-dimethyl-N-(pyrazon-1-yl-methyl)-2-chloroacetanilide

2,6-dimethyl-N-(4-methylpyrazol-1-methyl)-2-chloro-acetanilide

2,6-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-2-chloroacetanilide

2,6-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-2-chloroacetanilide

2,6-dimethyl-N-(1,3-dioxolan-2-yl-methyl)-2-chloroacetanilide

2,6-dimethyl-N-(2-methoxyethyl)-2-chloroacetanilide

2,6-dimethyl-N-isobutoxymethyl-2-chloroacetanilide

2,6-diethyl-N-methoxymethyl-2-chloroacetanilide

2,6-diethyl-N-n-butoxymethyl-2-chloroacetanilide

2,6-diethyl-N-ethoxycarbonylmethyl-2-chloroacetanilide

2,3,6-trimethyl-N-(pyrazol-1-yl-methyl)-2-chloroacetanilide

2,3-dimethyl-N-isopropyl-2-chloroacetanilide

2,6-diethyl-N-(propoxyethyl)-2-chloroacetanilide

2-(2-methyl-4-chlorophenoxy-N-methoxyacetamide

2-(-naphthoxy)-N,N-diethylpropionamide

2,2-diphenyl-N,N-dimethylacetamide

α-(3,4,5-tribromopyrazol-1-yl)-N,N-dimethylpropionamide

N-(1,1-dimethylpropynyl)-3,5-dichlorobenzamide

N-1-naphthylphthalamic acid

propionic acid 3,4-dichloroanilide

cyclopropanecarboxylic acid 3,4-dichloroanilide

methacrylic acid 3,4-dichloroanilide

2-methylpentanecarboxylic acid 3,4-dichloroanilide

5-acetamido-2,4-dimethyltrifluoromethanesulfone anillide

5-acetamido-4-methyltrifluoromethanesulfone anilide

2-propionylamino-4-methyl-5-chlorothiazole

O-(methylsulfonyl)-glycolic acid N-ethoxymethyl-2,6-dimethylanilide

O-(methylaminosulfonyl)-glycolic acid N-isopropylanilide

O-(isopropylaminosulfonyl)-glycolic acid N-but-1-yn-3-yl-anilide

O-(methylaminosulfonyl)-glycolic acid hexamethyleneamide

2,6-dichlorothiobenzamide

2,6-dichlorobenzonitrile

3,5-dibromo-4-hydroxybenzonitrile (salts)

3,5-diiodo-4-hydroxybenzonitrile (salts)

3,5-dibromo-4-hydroxy-O-2,4-dinitrophenylbenzaldoxime (salts)

3,5-dibromo-4-hydroxy-O-2-cyano-4-nitrophenylbenzaldoxime (salts)

pentachlorophenol, sodium salt

2,4-dichlorophenyl-4'-nitrophenyl ether

2,4,6-trichlorophenyl-4'-nitrophenyl ether

2-fluoro-4,6-dichlorophenyl-4'-nitrophenyl ether

2-chloro-4-trifluoromethylphenyl-4'-nitrophenyl ether

2,4'-dinitro-4-trifluoromethyl-diphenyl ether

2,4-dichlorophenyl-3'-methoxy-4'-nitro-phenyl ether

2-chloro-4-trifluoromethylphenyl-3'-ethoxy-4'-nitro-phenyl ether

2-chloro-4-trifluoromethylphenyl-3'-carboxy-4'-nitro-phenyl ether (salts)

2,4-dichlorophenyl-3'-methoxycarbonyl-4'-nitro-phenyl ether

2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione

2-(3-tert.butylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione

2-(3-isopropylcarbamoyloxyphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione

2-phenyl-3,1-benzoxazinone-(4)

(4-bromophenyl)-3,4,5,9,10-pentaazatetracyclo-[5,4,1,0²,6, 0,⁸,11 ]-dodeca-3,9-diene

2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranylmethane sulfonate

2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyldimethylaminosulfate

2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl-(N-methyl-N-acetyl)-aminosulfonate

3,4-dichloro-1,2-benzisothiazole

N-4-chlorophenyl-allylsuccinimide

2-methyl-4,6-dinitrophenol (salts, esters)

2-sec.butyl-4,6-dinitrophenol (salts, esters)

2-sec.butyl-4,6-dinitrophenol acetate

2-tert.butyl-4,6-dinitrophenol acetate

2-tert.butyl-4,6-dinitrophenol (salts)

2-tert.butyl-5-methyl-4,6-dinitrophenol (salts)

2-tert.butyl-5-methyl-4,6-dinitrophenol acetate

2-sec.amyl-4,6-dinitrophenol (salts, esters)

1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)-urea

1-phenyl-3-(2-methylcyclohexyl)-urea

1-phenyl-1-benzoyl-3,3-dimethylurea

1-(4-chlorophenyl)-1-benzoyl-3,3-dimethylurea

1-(4-chlorophenyl)-3,3-dimethylurea

1-(4-chlorophenyl)-3-methyl-3-but-1-yn-3-yl-urea

1-(3,4-dichlorophenyl)-3,3-dimethylurea

1-(3,4-dichlorophenyl)-1-benzoyl-3,3-dimethylurea

1-(3,4-dichlorophenyl)-3-methyl-3-n.butylurea

1-(4-isopropylphenyl)-3,3-dimethylurea

1-(3-trifluoromethylphenyl)-3,3-dimethylurea

1-(3-α,α,β,β-tetrafluoroethoxyphenyl)-3,3-dimethylure

1-(3-tert.butylcarbamoyloxyphenyl)-3,3-dimethylurea

1-(3-chloro-4-methylphenyl)-3,3-dimethylurea

1-(3-chloro-4-methoxyphenyl)-3,3-dimethylurea

1-(3,5-dichloro-4-methoxyphenyl)-3,3-dimethylurea

1-[4-(4'-chlorophenoxy)-phenyl]-3,3-dimethylurea

1-[4-(4'-methoxyphenoxy)-phenyl]-3,3-dimethylurea

1-cyclooctyl-3,3-dimethylurea

1-(hexahydro-4,7-methanoindan-5-yl)-3,3-dimethylurea

1-[1- or 2-(3a,4,5,7,7a-hexahydro)-4,7-methanoindanyl]-3,3-dimethylurea

1-(4-fluorophenyl)-3-carboxymethoxy-3-methylurea

1-phenyl-3-methyl-3-methoxyurea

1-(4-chlorophenyl)-3-methyl-3-methoxyurea

1-(4-bromophenyl)-3-methyl-3-methoxyurea

1-(3,4-dichlorophenyl)-3-methyl-3-methoxyurea

1-(3-chloro-4-bromophenyl)-3-methyl-3-methoxyurea

1-(3-chloro-4-isopropylphenyl)-3-methyl-3-methoxyurea

1-(3-chloro-4-methoxyphenyl)-3-methyl-3-methoxyurea

1-(3-tert.butylphenyl)-3-methyl-3-methoxyurea

1-(2-benzthiazolyl)-1,3-dimethylurea

1-(2-benzthiazolyl)-3-methylurea

1-(5-trifluoromethyl-1,3,4-thiadiazolyl)-1,3-dimethylurea

imidazolidin-2-one-1-carboxylic acid isobutylamide

1,2-dimethyl-3,5-diphenylpyrazolium-methylsulfate

1,2,4-trimethyl-3,5-diphenylpyrazolium-methylsulfate

1,2-dimethyl-4-bromo-3,5-diphenylpyrazolium-methylsulfate

1,3-dimethyl-4-(3,4-dichlorobenzoyl)-5-(4-methylphenylsulfonyloxy)-pyrazole

2,3,5-trichloropyridinol-(4)

1-methyl-3-phenyl-5-(3'-trifluoromethylphenyl)-pyridone-(4)

1-methyl-4-phenylpyridinium chloride

1,1-dimethylpyridinium chloride

3-phenyl-4-hydroxy-6-chloropyridazine

1,1'-dimethyl-4,4'-dipyridylium-di(methylsulfate)

1,1-di-(3,5-dimethylmorpholine-carbonylmethyl)-4,4'-dipyridylium dichloride

1,1'-ethylene-2,2'-dipyridylium dibromide

3-[1-(N-ethoxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione

3-[1-(N-allyloxyamino)-propylidene]-6-ethyl-3,4-dihydro-2H-pyran-2,4-dione

2-[1-(N-allyloxyamino)-propylidene]-5,5-dimethylcyclohexane-1,3-dione (salts)

2-[1-(N-allyloxyamino-butylidene]-5,5-dimethylcyclohexane-1,3-dione (salts)

2-[1-(N-allyloxyamino-butylidene]-5,5-dimethyl-4-methoxycarbonyl-cyclohexane-1,3-dione (salts)

2-chlorophenoxyacetic acid (salts, esters, amides)

4-chlorophenoxyacetic acid (salts, esters, amides)

2,4-dichlorophenoxyacetic acid (salts, esters, amides)

2,4,5-trichlorophenoxyacetic acid (salts, esters, amides)

2-methyl-4-chlorophenoxyacetic acid (salts, esters, amides)

3,5,6-trichloro-2-pyridinyl-oxyacetic acid (salts, esters, amides)

2-chloro-4-trifluoromethyl-3'-ethoxycarbonyl-4'-nitrophenyl ether

1-(4-benzyloxyphenyl)-3-methyl-3-methoxyurea

2-[1-(2,5-dimethylphenyl)-ethylsulfonyl]-pyridine-N-oxide

1-acetyl-3-anilino-4-methoxycarbonyl-5-methylpyrazole

3-anilino-4-methoxycarbonyl-5-methylpyrazole

3-tert.butylamino-4-methoxycarbonyl-5-methylpyrazole

N-benzyl-N-isopropyl-trimethylacetamide

methyl 2-[4-(4'-chlorophenoxymethyl)-phenoxy]-propionate

ethyl 2-[4-(5'-bromopyridyl-2-oxy)-phenoxy]-propionate

ethyl 2-[4-(5'-iodopyridyl-2-oxy)-phenoxy]-propionate

n-butyl 2-[4-(5'-iodopyridyl-2-oxy)-phenoxy]-propionate

2-chloro-4-trifluoromethylphenyl-3'-(2-fluoroethoxy)-4'-nitrophenyl ether

2-chloro-4-trifluoromethylphenyl-3-(ethoxycarbonyl)-methyl-thio-4-nitrophenyl ether

2,4,6-trichlorophenyl-3-(ethoxycarbonyl)-methylthio-4-nitro-phenyl ether

2-[1-(N-ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-3-hydroxy-cyclohex-2-en-1-one (salts)

2-[1-(N-ethoxamino)-butylidene]-5-(2-phenylthiopropyl)-3-hydroxy-cyclohex-2-en-1-one (salts)

ethyl 4-[4-(4'-trifluoromethyl)-phenoxy]-pentene-2-carboxylate

2-chloro-4-trifluoromethyl-3'-methoxycarbonyl-4'-nitrophenyl ether

2,4-dichlorophenyl-3'-carboxy-4'-nitrophenyl ether (salts)

4,5-dimethoxy-2-(3-α,α,β-trifluoro-β-bromoethoxyphenyl)-3-(2H)-pyridazinone

2,4-dichlorophenyl-3'-ethoxy-ethoxy-ethoxy-4'-nitrophenyl ether

2,3-dihydro-3,3-dimethyl-5-benzofuranyl-ethane sulfonate

N-[4-methoxy-6-methyl-1,3,5-triazin-2-yl-aminocarbonyl]-2-chlorobenzene sulfonamide

1-(3-chloro-4-ethoxyphenyl)-3,3-dimethylurea

ethyl 2-methyl-4-chlorophenoxy-thioacetate

2-chloro-3,5-diiodo-4-acetoxy-pyridine

1-(4-[2-(4-methylphenyl)-ethoxy]-phenyl-3-methyl-3-methoxyurea.

It may also be useful to apply the active ingredients, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added. 

We claim:
 1. An aralkylphenylurea of the formula ##STR43## wherein A is n-propylene or n-butylene, R¹ is methyl, R² is methyl or methoxy, Y is hydrogen or chlorine, Z is hydrogen or alkyl of 1 to 4 carbon atoms and n is
 1. 2. A process for combating the growth of unwanted plants, wherein the plants or the soil are treated with a herbicidally effective amount of an aralkylphenylurea of the formula ##STR44## wherein A is n-propylene or n-butylene, R¹ is methyl, R² is methyl or methoxy, Y is hydrogen or chlorine, Z is hydrogen or alkyl of 1 to 4 carbon atoms and n is
 1. 3. A compound as set forth in claim 1 selected from the group consisting ofN'-3-(3-phenylpropyl)-phenyl-N,N-dimethylurea, N'-3-(3-phenylpropyl)-phenyl-N-methoxy-N-methylurea, N'-3-(3-(4-methylphenyl)-propyl)-phenyl-N-methoxy-N-methylurea, and N'-4-(3-(4-methylphenyl)-propyl)-phenyl-N-methoxy-N-methylurea. 